Author(s)

Jessica J. Sánchez García¹, Alberto D. Hernández-Suzan¹, Elena Martínez-Klimova¹, Marcos Flores-Alamo¹, Teresa Ramírez Apan², Elena I. Klimova^1*

¹Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México.
²Instituto de Química, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México.

A novel 2-indano[2,3b]-2-ferrocenyl- and 2-indano[2,3b]-2-(p-methoxy-phenyl)[1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl- and 2-(p-methoxyphenyl)[1,4] benzothiazine 4a,b (addition “anti-Michael”/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxy-phenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new “anti-Michael” addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported. As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, ¹H and ¹³C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.

Ferrocene, Addition “Anti-Michael”, Reaction Cyclization, 1, 5-Thiazepines, 1, 4-Thiazines, Antitumor Cell Lines

García, J. , Hernández-Suzan, A. , Martínez-Klimova, E. , Flores-Alamo, M. , Apan, T. and Klimova, E. (2017) “Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol. International Journal of Organic Chemistry, 7, 57-81. doi: 10.4236/ijoc.2017.71006.